EP2402369B1 - Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire - Google Patents

Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire Download PDF

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Publication number
EP2402369B1
EP2402369B1 EP11175264.8A EP11175264A EP2402369B1 EP 2402369 B1 EP2402369 B1 EP 2402369B1 EP 11175264 A EP11175264 A EP 11175264A EP 2402369 B1 EP2402369 B1 EP 2402369B1
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EP
European Patent Office
Prior art keywords
seq
collagen
tetrapeptide
composition
peptides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP11175264.8A
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German (de)
English (en)
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EP2402369A3 (fr
EP2402369A2 (fr
Inventor
Scott Harris
Timothy Falla
Lijuan Zhang
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Helix Biomedix Inc
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Helix Biomedix Inc
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Publication date
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Priority to EP15188894.8A priority Critical patent/EP3002294B8/fr
Priority to PL15188894T priority patent/PL3002294T3/pl
Priority to PL11175264T priority patent/PL2402369T3/pl
Publication of EP2402369A2 publication Critical patent/EP2402369A2/fr
Publication of EP2402369A3 publication Critical patent/EP2402369A3/fr
Application granted granted Critical
Publication of EP2402369B1 publication Critical patent/EP2402369B1/fr
Priority to CY20151101181T priority patent/CY1117084T1/el
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin, cold insoluble globulin [CIG]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07—Tetrapeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00—Preparations for use in therapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Definitions

  • ECM proteins can stimulate useful elements in skin, such as type I collagen, type III collagen, and fibronectin ( Katayama et. al., J. BIOL. CHEM. 288:9941-9944 (1983 )).
  • Katayama et al. identified the pentapeptide, KTTKS (SEQ ID NO:17), within the carboxy-terminal propeptide (residues 197-241) of type I collagen.
  • the propeptide is cleaved during production of the mature collagen protein.
  • the cleaved propeptide may participate in regulating collagen production via a biosynthesis feedback mechanism, with the KTTKS segment playing an active role.
  • Maquart et al. J Soc BIOL.
  • REPLIKINESTM The disclosed sequences are referred to as REPLIKINESTM.
  • REPLIKINE is defined as a short sequence within ECM proteins that occurs multiple times (i.e., is replicated). This sequence may be present in one ECM protein (e.g., collagen IV). Preferably, the sequence is present in multiple ECM proteins (e.g., all collagens, elastin, laminin, etc.). The presence of the sequence in multiple ECM proteins increases the likelihood that the fragment may be able to promote ECM synthesis or repair.
  • H12 appears one residue (or frame) shift from the GxxG tetrapeptide GGAG in Collagen III (SEQ ID NO:46) as illustrated in Figure 2 .
  • all frame shift active sequences are bold and underlined and the GxxG sequences occurring one frame shift away are double-underlined.
  • this tetrapeptide achieves good results for collagen production at 48 hours.
  • sequence PGPR which is H10 (SEQ ID NO:4) which occurs eleven times in Collagens I-IV.
  • the formulations would induce synthesis of ECM for the entire 48 hour period such that more collagen is produced by 48 hours than at 24 hours.
  • tetrapeptides that promote production of ECM proteins at 24 hours, but show diminished production at 48 hours, are less favored.
  • Table 6 shows the results of the currently disclosed peptides. Preferred peptides are in bold.
  • Table 6 Disclosed peptides SEQ ID NO Peptides Released collagen ( ⁇ g/mL) 24h Released collagen ( ⁇ g/mL) 48h Significant release of collagen at 24h and 48h Increase in collagen release at 48h v. 24h Decrease in collagen release at 48h v.
  • Table 7 Effect of peptides on human skin epithelial wound closure in vitro 0hr 6hr 10hr Compound W-size* W-size % closure W-size % closure PBS-1 36 29 19.40% 21 41.70% PBS-2 52 42 19.20% 30 42.30% SEQ ID NO:14 25 12 52% 2.75 89% SEQ ID NO:5 48 39 19% 30 37.50% *W-size: wound size (arbitrary)

Claims (14)

  1. Tétrapeptide comprenant SEQ ID n° : 1 (PEGP) destiné à être utilisé comme médicament.
  2. Tétrapeptide comprenant SEQ ID n° : 1 (PEGP) destiné à être utilisé comme médicament pour le traitement de peau endommagée ou en maintien de peau saine.
  3. Utilisation d'un tétrapeptide comprenant SEQ ID n° : 1 (PEGP) comme produit cosmétique.
  4. Tétrapeptide selon la revendication 1 ou 2 ou utilisation d'un tétrapeptide selon la revendication 3, le tétrapeptide étant amidé à l'extrémité carboxy.
  5. Composition pharmaceutique destinée à être utilisée comme médicament comprenant un tétrapeptide comprenant SEQ ID n° : 1 (PEGP) et un vecteur pharmaceutiquement acceptable.
  6. Composition destinée à être utilisée selon la revendication 5, le tétrapeptide étant présent en une concentration efficace allant d'environ 0,01 µg/ml à environ 100 µg/ml et de préférence encore allant d'environ 0,1 µg/ml à environ 1 µg/ml.
  7. Composition destinée à être utilisée selon la revendication 5 ou 6, la composition étant sous la forme d'un aérosol, d'une émulsion, d'un liquide, d'une lotion, d'une crème, d'une pâte, d'un onguent ou d'une mousse.
  8. Composition destinée à être utilisée selon l'une quelconque des revendications 5 à 7 destinée à être utilisée en traitement de soins de la peau.
  9. Procédé in vitro pour la stimulation de la production de collagène par une cellule, le procédé comprenant l'exposition d'une cellule à un tétrapeptide comprenant SEQ ID n° : 1 (PEGP) ce qui induit de cette manière la production de collagène par la cellule.
  10. Procédé selon la revendication 9, la cellule étant une cellule fibroblaste.
  11. Composition destinée à être utilisée selon l'une quelconque des revendications 5 à 8, le tétrapeptide étant utile pour stimuler la production de collagène lorsqu'il est appliqué à la peau.
  12. Composition destinée à être utilisée selon la revendication 8, ledit traitement de soins de la peau s'adressant à la formation de rides, la tonification, le raffermissement et l'affaissement de la peau.
  13. Composition destinée à être utilisée selon l'une quelconque des revendications 5 à 8 destinée à être utilisée en réduction de la formation de cicatrices sur de la peau endommagée par le vieillissement normal, une maladie, une blessure, un traumatisme ou une chirurgie.
  14. Composition destinée à être utilisée selon la revendication 13, ladite utilisation comprenant l'administration de la composition à la plaie d'un animal.
EP11175264.8A 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire Active EP2402369B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP15188894.8A EP3002294B8 (fr) 2006-06-13 2007-06-12 Fragments peptidiques pour induire la synthèse de protéines de la matrice extracellulaire
PL15188894T PL3002294T3 (pl) 2006-06-13 2007-06-12 Fragmenty peptydowe do indukowania syntezy białek macierzy zewnątrzkomórkowej
PL11175264T PL2402369T3 (pl) 2006-06-13 2007-06-12 Fragmenty peptydów do indukowania syntezy białek macierzy zewnątrzkomórkowej
CY20151101181T CY1117084T1 (el) 2006-06-13 2015-12-22 Θραυσματα πεπτιδιου για την επαγωγη συνθεσης πρωτεϊνων εξωκυτταριας μητρας

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81328406P 2006-06-13 2006-06-13
EP07796001A EP2027152B1 (fr) 2006-06-13 2007-06-12 Fragments peptidiques destinés à induire la synthèse de protéines matricielles extracellulaires

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
EP07796001.1 Division 2007-06-12
EP07796001A Division EP2027152B1 (fr) 2006-06-13 2007-06-12 Fragments peptidiques destinés à induire la synthèse de protéines matricielles extracellulaires

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP15188894.8A Division-Into EP3002294B8 (fr) 2006-06-13 2007-06-12 Fragments peptidiques pour induire la synthèse de protéines de la matrice extracellulaire
EP15188894.8A Division EP3002294B8 (fr) 2006-06-13 2007-06-12 Fragments peptidiques pour induire la synthèse de protéines de la matrice extracellulaire

Publications (3)

Publication Number Publication Date
EP2402369A2 EP2402369A2 (fr) 2012-01-04
EP2402369A3 EP2402369A3 (fr) 2012-05-16
EP2402369B1 true EP2402369B1 (fr) 2015-11-25

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ID=38664422

Family Applications (5)

Application Number Title Priority Date Filing Date
EP11175264.8A Active EP2402369B1 (fr) 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire
EP15188894.8A Active EP3002294B8 (fr) 2006-06-13 2007-06-12 Fragments peptidiques pour induire la synthèse de protéines de la matrice extracellulaire
EP07796001A Active EP2027152B1 (fr) 2006-06-13 2007-06-12 Fragments peptidiques destinés à induire la synthèse de protéines matricielles extracellulaires
EP15167681.4A Withdrawn EP2940042A3 (fr) 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire
EP11175263.0A Active EP2409988B1 (fr) 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire

Family Applications After (4)

Application Number Title Priority Date Filing Date
EP15188894.8A Active EP3002294B8 (fr) 2006-06-13 2007-06-12 Fragments peptidiques pour induire la synthèse de protéines de la matrice extracellulaire
EP07796001A Active EP2027152B1 (fr) 2006-06-13 2007-06-12 Fragments peptidiques destinés à induire la synthèse de protéines matricielles extracellulaires
EP15167681.4A Withdrawn EP2940042A3 (fr) 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire
EP11175263.0A Active EP2409988B1 (fr) 2006-06-13 2007-06-12 Fragments de peptides pour induire la synthèse de protéines de matrice extracellulaire

Country Status (19)

Country Link
US (5) US8110658B2 (fr)
EP (5) EP2402369B1 (fr)
JP (2) JP5535620B2 (fr)
CN (2) CN104017071B (fr)
AT (1) ATE533785T1 (fr)
AU (1) AU2007258387B2 (fr)
BR (2) BR122018002612B8 (fr)
CA (4) CA2947353A1 (fr)
CY (1) CY1112241T1 (fr)
DK (3) DK2409988T3 (fr)
ES (4) ES2680022T3 (fr)
HK (5) HK1128700A1 (fr)
HU (2) HUE026698T2 (fr)
MX (2) MX361694B (fr)
PL (4) PL2409988T3 (fr)
PT (2) PT2402369E (fr)
RU (2) RU2501807C2 (fr)
SI (2) SI2027152T1 (fr)
WO (1) WO2007146269A2 (fr)

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SG11201505538QA (en) * 2013-02-14 2015-08-28 Helix Biomedix Inc Short bio-active peptides for promoting wound healing
WO2014140890A2 (fr) 2013-03-13 2014-09-18 Neocutis Sa Peptides pour le rajeunissement de la peau et leurs procédés d'utilisation
US10392611B2 (en) 2013-05-30 2019-08-27 Duke University Polymer conjugates having reduced antigenicity and methods of using the same
US10364451B2 (en) 2013-05-30 2019-07-30 Duke University Polymer conjugates having reduced antigenicity and methods of using the same
HUE032970T2 (en) 2013-06-14 2017-11-28 Helix Biomedix Inc Tetrapeptides from human C-X-C chemonics for the treatment of various skin diseases
US10385115B2 (en) 2015-03-26 2019-08-20 Duke University Fibronectin type III domain-based fusion proteins
MX2018001511A (es) 2015-08-04 2018-08-01 Univ Duke Polimeros furtivos desordenados de forma intrinseca codificados geneticamente para suministro y metodos para usar los mismos.
KR101916522B1 (ko) 2015-09-25 2018-11-08 경상대학교산학협력단 굴 가수분해물의 제조방법 및 이로부터 분리된 펩타이드
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CN109890833A (zh) * 2016-09-14 2019-06-14 杜克大学 用于递送亲水性药物的基于三嵌段多肽的纳米粒子
US11155584B2 (en) 2016-09-23 2021-10-26 Duke University Unstructured non-repetitive polypeptides having LCST behavior
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US11554097B2 (en) 2017-05-15 2023-01-17 Duke University Recombinant production of hybrid lipid-biopolymer materials that self-assemble and encapsulate agents
US11680083B2 (en) 2017-06-30 2023-06-20 Duke University Order and disorder as a design principle for stimuli-responsive biopolymer networks
WO2020028806A1 (fr) 2018-08-02 2020-02-06 Duke University Protéines de fusion à double agoniste
US11512314B2 (en) 2019-07-12 2022-11-29 Duke University Amphiphilic polynucleotides
EP4000597A1 (fr) * 2020-11-17 2022-05-25 The Boots Company plc Tétrapeptide et compositions comprenant des tétrapeptides
EP4000596A1 (fr) * 2020-11-17 2022-05-25 The Boots Company plc Tétrapeptide et compositions comprenant des tétrapeptides
EP4000595A1 (fr) * 2020-11-17 2022-05-25 The Boots Company plc Tétrapeptide et compositions comprenant des tétrapeptides
EP4000598A1 (fr) * 2020-11-17 2022-05-25 The Boots Company plc Tétrapeptide et compositions comprenant des tétrapeptides
EP4140473A1 (fr) * 2021-08-27 2023-03-01 The Boots Company plc Compositions cosmétiques
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